Monolayer nanosheets formed by liquid exfoliation of charge-assisted hydrogen-bonded frameworks

Nicks, Joshua; Boer, Stephanie; White, Nicholas G.; Foster, Jonathan A.

doi:10.1039/d0sc06906j

Cited by 41 publications

(45 citation statements)

References 66 publications

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“…As chloride anions are potentially coordinating and may interfere with the self-assembly process, we exchanged these for non-coordinating BPh 4 -anions in quantitative yield. We attempted to prepare 2 31 in an analogous manner using a Suzuki coupling of tris-bromomethyl compound 5 [36] and 4-cyanophenylboronic acid in conditions similar to those reported by Kotha et al [37] We were able to prepare the new tris-nitrile 6, albeit in relatively low yield (27 %). However, attempts to convert this into the tris-amidinium 2 31 were unsuccessful with a mixture of products being observed: mass spectrometry and NMR spectroscopy indicated that some product was formed but we were not able to isolate this or drive the reaction to completion.…”

Section: Synthesis Of Tectonsmentioning

confidence: 88%

“…Before attempting to synthesise our cage systems, we used semiempirical calculations with PM6 parameters [34] to determine if our proposed systems were geometrically feasible. We initially proposed the tris-amidinium compounds 1 31 and 2 31 as these appeared relatively easy to synthesise and appeared to have the correct geometry to assemble into cages with terephthalate (TP 2-) and isophthalate (IP 2-) anions, respectively. As can be seen in Fig.…”

Section: Design Of Cage Systemsmentioning

confidence: 99%

“…The tetraphenylmethane based tecton 1 31 was synthesised from the known tris-alkyne 3, [35] as shown in Scheme 1. Sonogashira coupling of 3 with 3-iodobenzonitrile gave tris-nitrile 4; subsequent reaction with lithium bis(trimethylsilyl)amide in THF followed by workup with ethanolic HCl gave 1 .…”

Section: Synthesis Of Tectonsmentioning

confidence: 99%

“…Given our inability to synthesise 2 31 , we next investigated whether it was possible to prepare the tris-carboxylate 7 3-. We reasoned that it would be possible to synthesise a cage from this and the bis-benzamidinium 8 21 , which would in effect be the 'reverse' of the initially proposed 2 2 .…”

Section: Synthesis Of Tectonsmentioning

confidence: 99%

“…[26][27][28] These hydrogen bonds can be quite strong and survive in polar solvents or even water: indeed we have reported hydrogen bonded frameworks based on this interaction that can be formed in water, [29] and can withstand heating in water for extended periods (days). [30,31] As well as investigating framework formation using the amidiniumÁÁÁcarboxylate interaction, we have been investigating whether this interaction can be used to prepare selfassembled cages. Specifically, we envisaged designing a trisamidinium compound with an appropriate geometry to assemble around dicarboxylate anions such as terephthalate or isophthalate.…”

Section: Introductionmentioning

confidence: 99%

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An Investigation of Five Component [3+2] Self-Assembled Cage Formation Using Amidinium···Carboxylate Hydrogen Bonds

et al. 2021

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The assembly of hydrogen bonded cages using amidiniumÁÁÁcarboxylate hydrogen bonding interactions was investigated. A new tris-amidinium hydrogen bond donor tecton based on a tetraphenylmethane scaffold was prepared and its selfassembly with the terephthalate anion studied, and a new tricarboxylate hydrogen bond acceptor tecton was synthesised and its assembly with the 1,3-benzenebis(amidinium) hydrogen bond donor explored. In both cases, molecular modelling indicated that the formation of the cages was geometrically feasible and 1 H NMR spectroscopic evidence was consistent with interactions between the components in competitive d 6 -DMSO solvent mixtures. DOSY NMR spectroscopy of both systems indicated that both components diffuse at the same rate as each other, and diffusion coefficients were consistent with cage formation, and with the formation of assemblies significantly larger than the individual components. An X-ray crystal structure showed that one of the assemblies did not have the desired cage structure in the solid state.

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Section: Synthesis Of Tectonsmentioning

confidence: 88%

Section: Design Of Cage Systemsmentioning

confidence: 99%

Section: Synthesis Of Tectonsmentioning

confidence: 99%

Section: Synthesis Of Tectonsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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An Investigation of Five Component [3+2] Self-Assembled Cage Formation Using Amidinium···Carboxylate Hydrogen Bonds

et al. 2021

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Self‐Assembling Anti‐Freezing Lamellar Nanostructures in Subzero Temperatures

Yin,

Guo,

Wang

et al. 2024

Advanced Science

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The requirement for cryogenic supramolecular self‐assembly of amphiphiles in subzero environments is a challenging topic. Here, the self‐assembly of lamellar lyotropic liquid crystals (LLCs) are presented to a subzero temperature of −70 °C. These lamellar nanostructures are assembled from specifically tailored ultra‐long‐chain surfactant stearyl diethanolamine (SDA) in water/glycerol binary solvent. As the temperature falls below zero, LLCs with a liquid‐crystalline Lα phase, a tilted Lβ phase, and a new folded configuration are obtained consecutively. A comprehensive experimental and computational study is performed to uncover the precise microstructure and formation mechanism. Both the ultra‐long alkyl chain and head group of SDA play a crucial role in the formation of lamellar nanostructures. SDA head group is prone to forming hydrogen bonds with water, rather than glycerol. Glycerol cannot penetrate the lipid layer, which mixes with water arranging outside of the lipid bilayer, providing an ideal anti‐freezing environment for SDA self‐assembly. Based on these nanostructures and the ultra‐low freezing point of the system, a series of novel cryogenic materials are created with potential applications in extremely cold environments. These findings would contribute to enriching the theory and research methodology of supramolecular self‐assembly in extreme conditions and to developing novel anti‐freezing materials.

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Structural Design and Energy and Environmental Applications of Hydrogen‐Bonded Organic Frameworks: A Systematic Review

Liu,

et al. 2024

Advanced Science

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Hydrogen‐bonded organic frameworks (HOFs) are emerging porous materials that show high structural flexibility, mild synthetic conditions, good solution processability, easy healing and regeneration, and good recyclability. Although these properties give them many potential multifunctional applications, their frameworks are unstable due to the presence of only weak and reversible hydrogen bonds. In this work, the development history and synthesis methods of HOFs are reviewed, and categorize their structural design concepts and strategies to improve their stability. More importantly, due to the significant potential of the latest HOF‐related research for addressing energy and environmental issues, this work discusses the latest advances in the methods of energy storage and conversion, energy substance generation and isolation, environmental detection and isolation, degradation and transformation, and biological applications. Furthermore, a discussion of the coupling orientation of HOF in the cross‐cutting fields of energy and environment is presented for the first time. Finally, current challenges, opportunities, and strategies for the development of HOFs to advance their energy and environmental applications are discussed.

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Monolayer nanosheets formed by liquid exfoliation of charge-assisted hydrogen-bonded frameworks

Abstract: We report the liquid-phase ultrasonic exfoliation of two layered hydrogen-bonded frameworks into monolayer, micron-sized, and water-stable nanosheets (HONs) connected purely by hydrogen-bonding interactions.

Cited by 41 publications

References 66 publications

An Investigation of Five Component [3+2] Self-Assembled Cage Formation Using Amidinium···Carboxylate Hydrogen Bonds

An Investigation of Five Component [3+2] Self-Assembled Cage Formation Using Amidinium···Carboxylate Hydrogen Bonds

Self‐Assembling Anti‐Freezing Lamellar Nanostructures in Subzero Temperatures

Structural Design and Energy and Environmental Applications of Hydrogen‐Bonded Organic Frameworks: A Systematic Review

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